


The First Time is always the kinkiest (Gay Pride Day)

by Shtwriter_yup_datsme



Series: Pride Month Oneshots! 🌈 [1]
Category: Supernatural
Genre: Dean Winchester Has a Panty Kink, Established Castiel/Dean Winchester, Gabriel is mentioned, Gay Pride, LGBTQ Themes, M/M, Smut, Supportive Sibling Sam Winchester
Language: English
Status: Completed
Published: 2020-06-01
Updated: 2020-06-01
Packaged: 2021-03-02 23:27:09
Rating: Not Rated
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 1,455
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/24485053
Author URL: https://archiveofourown.org/users/Shtwriter_yup_datsme/pseuds/Shtwriter_yup_datsme
Summary: Panty kink!
Relationships: Castiel/Dean Winchester
Series: Pride Month Oneshots! 🌈 [1]
Series URL: https://archiveofourown.org/series/1768747
Kudos: 16





	The First Time is always the kinkiest (Gay Pride Day)

**Author's Note:**

> Panty kink!

Ever since Cas came out as gay and in love with Dean the two have been more than happy, cuddling and sleeping in the same bed, it all came so natural to them except they haven't taken the big step

_The sex step_

They were kind of dancing around it, they'd done pretty much everything else but never actual sex, Cas was a virgin and Dean hadn't been with a guy in years

"Don't forget the pie!" Dean called after his boyfriend as Cas headed out to he store, the angel huffed "Love you too Dean"

Sam chuckled at the two and smiled, "So you two- are doing good huh?"

Dean eyed his brother "Yeah.. why?" Sam shrugged "Just wanted to know, I like seeing you happy Dean"

"I am"

They fell back into a comfortable silence, Sam was reading his nerd book and Dean tried to focus on his magazine "..We haven't had sex" He blurted suddenly

"What?"'

"Me and Cas..we haven't had sex yet- I mean it's not a big deal-"

"Sounds like it is" Sam said going full on therapist, "As much as I'm going to regret this.. but is it your first time with a guy?"

Dean cleared his throat "No.." He waited for Sam to react but he just patiently waited for Dean to continue "But it's Cas' first time ever, I want it to be awesome"

"You've never taken someone's virginty before?" Sam sounded surprised " _You_ 'Mr I can't keep it in my pants'?"

Dean fought the urge to roll his eyes "No I've never wanted that kind of responsibility, but Cas is different"

Sam sighed "Look Dean it's sex you've always been good at that, I'll make myself scarce for a couple hours when Cas gets back give you guys enough time to do whatever"

"What are you gonna do?"

Sam shrugged "Visit Gabe maybe" The archangel wasn't staying too far from Lebanon and they'd occasionally hang out, becoming somewhat friends

"You guys hooking up?" Dean teased, "It's not like that Jerk" Sam scoffed; him and Gabriel were strictly friends who just pretend that they don't have feelings for each other

"How do you feel about me and Cas?..you know the whole he's a guy thing?- you've never said anything about it"

Sam raised a brow "Should I have?" He asked genuinely "Dean you're still you- literally _nothing_ has changed"

"Thanks bitch"

~🌈~

Dean had a plan, -granted it was half assed- he had a plan, he made Sam leave early practically shoving his brother out the door

He went into his and Cas' bedroom, cleaning it up, he got some of Sam's new bath candles and lit them in the room turning off the lights

He put lube and water bottles on the nightstand and for the next part he needed some 'liquid courage' so he took a couple shots and headed back to the bedroom, he dug into the bottom drawer of the dresser and pulled out a buried part of his past

_Red lace panties_

"Fuck" He whispered he really hoped Cas would like them

~🌈~

When Cas got home he put the groceries away in the kitchen and when he was done he looked around Dean and Sam were nowhere to be found

Until he began to feel it- _to hear it_

_"Cas..Cas.."_

It was Dean, the angel followed the sound all the way to their bedroom and when he opened the door his mouth was agape

Dean was sprawled out on the bed, in lace panties his cock just peeking out of the top as he rubbed himself moaning Cas' name over and over

His head turned when he heard Cas open the door, "Hey angel"

Cas swallowed thickly "Dean" He choked out and Dean -much to Cas' displeasure- stopped touching himself, he stood from the bed and walked over to Cas, whispering in his ear "I don't want to wait anymore angel"

Cas couldn't move, though he wanted desperately to jump Dean, his boyfriend slowly pushed down his trenchcoat, and blazer letting them fall to the ground "Is this okay?" He asked, and Cas nodded letting Dean unbutton his dress shirt, he pulled the shirt off and added it to the trenchcoat pile

Cas' pants were next and after they'd gotten them off, he led Cas to the bed by his tie and they climed onto it "Dean I've never.."

"I know Cas, just do what feels good" Dean said and Cas nodded lightly, Dean layed back on the pillows- and pulled Cas on top of him, they kissed making out feverishly

They'd done this many times before, sometimes naked others not- the first time was always the scariest and Cas was trying not to be too nervous as he felt his dick start to harden, his clothed erection rubbing against Dean's red panties

The angel groaned and grinded his hips down, "Oh fuck yes" Dean threw his head back into the pillows, "More" He begged, before Cas had showed up he'd barley touched himself just teasing his cock, but when Cas entered the room all self control flew out the window

"Need you Castiel"

Cas moaned at the sound of his full name falling from Dean's lips, he snaked his way down Dean's body and pushed his legs up, "You look so pretty in these Dean" Cas said pulling at the panties, he rubbed Dean through the soft satin lace "So beautiful"

Dean melted at the praise precum leaking onto his stomach, Cas dragged his panties down to his ankles, spreading his legs apart

Dean gave him the lube and Cas put some on his fingers, he wasn't really sure of what he was doing but when he got the first finger inside Dean and curled it making Dean whimper out a moan he knew he was doing must've felt good

Cas soon added a second finger and began thrusting them in and out of Dean's hole, Dean was livid he rolled his hips down impatiently "Babe- c'mon I'm ready"

Cas rolled his eyes at how impatient Dean was being "Dean, if you don't wait until I'm done you won't get to cum at all"

Dean eyed Cas carefully "You wouldn't" Cas pulled his fingers out and was on his knees, two black wings spreading out from behind him "You sure about that?"

The gulp that came from Dean was more than audible, Cas grinned "Good" He went back to fingering Dean- this time adding a third finger, Dean grunted wanting so badly to beg for more but he wasn't about to test Cas

Finally Cas was done stretching him out, with a thought his boxers disappeared and he rubbed his cock, he pressed his length against Dean's puffy rim slowly pushing past his entrance

Dean sucked in a hard breath because damn Cas was big, but he just enjoyed being full of his angel, as Cas bottomed out so many new sensations hit him, Dean was so tight and his hole clamped down on Cas' cock hard

Dean's hole swallowed his cock and it felt so fucking amazing, his wings fluttered and began to drip wing oil- he flushed slightly, it was all so new to him

"Dean..you feel so good, perfect" Cas gave a hard thrust and Dean nodded frantically, he gripped the blue tie that was still around Cas' neck and pulled him down into a kiss

His hands took in a fistful of soft feathers and to Dean's extreme surprise Cas lost it, his movements were fast never once slowing as he pounded away at Dean's ass

He had no idea how sensitive angel wings were but by the way Cas was acting they must've been _real_ sensitive, he rubbed them some more and Cas wrapped a hand around his erection, jerking Dean off

Dean's back arched off the bed, and in the distance he heard the a few of the lights in the bunkers burst, Cas was definitely close "Dean.." He moaned into Dean's neck as his hips sped "Come on- Cas fill me up!"

The angel's wings spasmed and he was cumming inside of Dean with soft grunts as Dean came all over his fist and stomach

Cas' rolled his shoulders back and his wings were gone, "Are you okay Dean?' He asked, and Dean nodded lazily "Yeah sure..I'm great.. _really_ _great_ " He smiled "What about you?- your first time was pleasurable I hope?"

Cas smiled back at him cuddling into Dean's chest "It was perfect" Dean sighed "We should probably clean up"

The angel pursed his lips "Or..you could rest up and we could go for round 2?" Dean smiled "Y'know what?- I think I might like that option better"

~🌈~

**Author's Note:**

> I know this wasn't really gay pride but..it was gay so..
> 
> BUT!
> 
> Don't worry I shall post a new chapter everyday for each day of pride! 
> 
> Ciao🌈


End file.
